US5449835A - Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) - Google Patents
Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) Download PDFInfo
- Publication number
- US5449835A US5449835A US08/339,140 US33914094A US5449835A US 5449835 A US5449835 A US 5449835A US 33914094 A US33914094 A US 33914094A US 5449835 A US5449835 A US 5449835A
- Authority
- US
- United States
- Prior art keywords
- bdnpf
- reaction solution
- dinitropropanol
- synthesizing
- acid catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Definitions
- the present invention relates to synthesis of bis(2,2-dinitropropyl)formal (BDNPF) without the use of a solvent medium.
- BDNPF Bis(2,2-dinitropropyl)formal
- BDNPF is an energetic plasticizer used in propellant and explosive applications. Because BDNPF is a solid at room temperature, BDNPF is usually combined with liquid bis(2,2-dinitropropyl)acetal (BDNPA) in a 50:50 weight percent mixture. The mixture of BDNPF and BDNPA is a liquid. BDNPA/BDNPF is a commercialized product.
- the use of a solvent in a chemical manufacturing process adds the need for solvent separation and waste disposal procedures.
- the current BDNPF manufacturing process has a high temperature (about 125° C.) vacuum evaporation step to remove the methylene chloride solvent and minor volatile byproduct impurities.
- Such evaporation not only increases manufacturing costs, but also represents a safety hazard by subjecting energetic materials to high temperatures.
- the present invention is directed to a process of synthesizing bis(2,2-dinitropropyl)formal (BDNPF).
- BDNPF bis(2,2-dinitropropyl)formal
- DNPOH 2,2-dinitropropanol
- a formaldehyde source in the presence a protic acid catalyst, such as H 2 SO 4 .
- H 2 SO 4 protic acid catalyst
- solid 2,2-dinitropropanol is mixed with a formaldehyde source to form a reaction solution.
- a slight stoichiometric excess of the formaldehyde source such that more than one mole of formaldehyde is present for every two moles of DNPOH, is preferably used in the reaction.
- typical formaldehyde sources include s-trioxane and paraformaldehyde.
- the formaldehyde source generates formaldehyde in situ for participation in the reaction with 2,2-dinitropropanol.
- a protic acid catalyst is then slowly added to the reaction solution.
- Protic acid catalysts are preferably selected from inorganic acids such as H 2 SO 4 , HCl, H 3 PO 4 , and HBr.
- the reaction solution is preferably maintained at a temperature below 30° C. and agitated.
- the reaction solution Upon completion of the reaction, the reaction solution is quenched with water. The water extracts the protic acid catalyst, water soluble reactants, and water soluble byproducts from the reaction solution. The reaction solution is then washed with an inorganic base solution, such as a hydroxide solution. Sufficient hydroxide is used to neutralize the protic acid catalyst and to solubilize unreacted 2,2-dinitropropanol as the nitronate salt, as well as any other aqueous soluble byproducts in the reaction solution. During the hydroxide wash, the pH is preferably kept sufficiently low to prevent hydrolysis of the BDNPF product. It is currently preferred to maintain the pH below 14 and preferably below 11.
- a low boiling temperature polar organic solvent which does not contain chlorine is added to extract the BDNPF product.
- Methyl tert-butyl ether (MTBE) is the currently preferred polar organic solvent.
- MTBE is able to extract BDNPF at sufficiently high purity such that the BDNPF product is usable for military applications without further purification, such as recrystallization or high temperature vacuum distillation.
- the exposure time and concentration of the inorganic base solution is preferably limited to prevent hydrolysis of the polar organic solvent.
- the aqueous phase is removed and discarded.
- the organic phase is washed with water.
- the organic solvent is evaporated to yield usable BDNPF product.
- the resulting yield is at least 60%, and preferably at least 70%, based on the starting quantity of 2,2-dinitropropanol.
- the evaporation is preferably accomplished at a temperature less than 60° C. and at a pressure less than about 150 mm Hg, and more preferably at a temperature less than 50° C. and at a pressure less than 20 mm Hg.
- the present invention is directed to a process of synthesizing bis(2,2-dinitropropyl)formal (BDNPF).
- BDNPF bis(2,2-dinitropropyl)formal
- DNPOH 2,2-dinitropropanol
- 2,2-dinitropropanol is mixed with a formaldehyde source to form a reaction solution.
- Typical formaldehyde sources include s-trioxane and paraformaldehyde.
- the formaldehyde source generates formaldehyde in situ for participation in the reaction with 2,2-dinitropropanol.
- the reaction is preferably carried out such that a slight stoichiometric excess of formaldehyde is produced by the formaldehyde source, that is, more than one mole of formaldehyde is present for every two moles of 2,2-dinitropropanol.
- a protic acid catalyst is then slowly added to the reaction solution.
- the protic acid catalyst is preferably selected from include H 2 SO 4 , HCl, H 3 PO 4 , and HBr.
- the protic acid catalyst participates in the reaction as a catalyst or dehydrating agent instead of a combinatorial reagent. That is, the acid catalyst does not combine with the 2,2-dinitropropanol or formaldehyde source to form the final BDNPF product.
- the reaction solution is preferably agitated.
- the reaction temperature during the protic acid catalyst addition is preferably from about -30° C. to 30° C., more preferably from about -10° C. to 10° C., and most preferably from about 0° C. to 5° C.
- the BDNPF product is produced at higher temperatures, as the temperature increases, an increasing amount of undesirable byproducts are also produced.
- low temperatures are preferred to inhibit hydrolysis of the BDNPF product by the protic acid catalyst.
- reaction solution Upon completion of the reaction, the reaction solution is quenched with water.
- the water extracts the protic acid catalyst, water soluble reactants, and water soluble byproducts from the reaction solution.
- the reaction solution is washed with an inorganic base solution, such as a hydroxide solution.
- the hydroxide concentration should be sufficient to neutralize the protic acid catalyst and to solubilize unreacted 2,2-dinitropropanol as the nitronate salt, as well as any other aqueous soluble byproducts in the reaction solution.
- the pH during the inorganic base wash is preferably kept sufficiently low to prevent hydrolysis of the BDNPF product. It is currently preferred to balance the amount of base solution used with its concentration such that the pH is maintained below about 11 during the initial base solution wash.
- the pH may be higher in a second base solution wash, but is preferably kept below 14.
- the hydroxide concentration may range from 1% to 25%, by weight.
- the hydroxide solution can be prepared from a number of different hydroxide salts known in the art, such as NaOH, KOH, and LiOH. A 5%, by weight, NaOH solution is currently preferred.
- the BDNPF product is extracted with a polar organic solvent which does not contain chlorine.
- Suitable solvents should have a boiling temperature below 125° C., preferably below 100° C., and most preferably below about 80° C., at ambient pressure.
- the organic solvent preferably does not react with the inorganic base under the exposure time and concentration conditions used in the process. It has been found that methyl tert-butyl ether (MTBE) is able to extract BDNPA at sufficiently high purity such that the BDNPA product is usable for military applications without further purification.
- MTBE methyl tert-butyl ether
- the aqueous phase is removed and discarded.
- the organic phase is washed with pure water to remove any remaining water soluble byproducts or reactants.
- the organic solvent is evaporated to yield usable BDNPF product.
- the resulting yield is at least 60%, and preferably at least 70%, based on the starting quantity of 2,2-dinitropropanol.
- the evaporation is preferably accomplished at a temperature less than 60° C. and at a pressure less than about 150 mm Hg, and more preferably at a temperature less than 50° C. and at a pressure less than 20 mm Hg.
- usable BDNPF product includes BDNPF of sufficient purity that a 50:50 mixture of BDNPA/BDNPF meets military density, refractive index and acid aging standards.
- the military specification for a 50:50 BDNPA/BDNPF mixture requires that the density be between 1.38-1.40 g/cc, the refractive index be between 1.462 and 1.464, and the acid aging test be below 0.5 mg KOH/g nitroplasticizer.
- the BDNPF nitroplasticizer is aged in an oven at 105° C. for 7 days. After aging, the sample is titrated with KOH to determine the acid content. The result is reported as mg KOH/g nitroplasticizer.
- BDNPF Bis(2,2-dinitropropyl)formal
- a NaOH solution was prepared by dissolving 2.9 g NaOH in 80 ml water, i.e., sufficient hydroxide to neutralize the H 2 SO 4 .
- the reaction products and the NaOH solution were cooled to 0° C., and the NaOH solution was added to the reaction products.
- the solid BDNPF was extracted with 3 ⁇ 30 ml of MTBE (methyl tert-butyl ether).
- MTBE methyl tert-butyl ether
- the MTBE solutions were combined and washed with 3 ⁇ 10 ml of 5%, by weight, NaOH solution followed by 3 ⁇ 10 ml H 20 washings.
- the aqueous phases were discarded and the organic phase dried with MgSO 4 .
- the MTBE was evaporated at 20° C. and less than 20 mm Hg, leaving 3.11 g (76% yield) usable BDNPF.
- Bis(2,2-dinitropropyl)formal is synthesized according to the procedure of Example 1 except that the protic acid catalyst is HCl instead of H 2 SO 4 .
- the protic acid catalyst is HCl instead of H 2 SO 4 .
- 2 ml of concentrated hydrochloric acid are used.
- BDNPF Bis(2,2-dinitropropyl)formal
- BDNPF Bis(2,2-dinitropropyl)formal
- the present invention provides a method for synthesizing BDNPF which does not use chlorinated solvents and which avoids costly and dangerous distillation procedures.
Abstract
Description
Claims (15)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/339,140 US5449835A (en) | 1994-11-14 | 1994-11-14 | Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) |
PCT/US1995/011371 WO1996015090A1 (en) | 1994-11-14 | 1995-09-08 | Synthesis of bis(2,2-dinitropropyl)formal (bdnpf) |
JP8516028A JPH10509450A (en) | 1994-11-14 | 1995-09-08 | Synthesis of bis (2,2-dinitropropyl) formal (BDNPF) |
EP95933058A EP0790972B1 (en) | 1994-11-14 | 1995-09-08 | Synthesis of bis(2,2-dinitropropyl)formal (bdnpf) |
CA002205227A CA2205227A1 (en) | 1994-11-14 | 1995-09-08 | Synthesis of bis(2,2-dinitropropyl)formal (bdnpf) |
DE69517535T DE69517535D1 (en) | 1994-11-14 | 1995-09-08 | SYNTHESIS OF BIS (2,2-DINITROPROPYL) FORMAL (BDNPF) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/339,140 US5449835A (en) | 1994-11-14 | 1994-11-14 | Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) |
Publications (1)
Publication Number | Publication Date |
---|---|
US5449835A true US5449835A (en) | 1995-09-12 |
Family
ID=23327687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/339,140 Expired - Lifetime US5449835A (en) | 1994-11-14 | 1994-11-14 | Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) |
Country Status (6)
Country | Link |
---|---|
US (1) | US5449835A (en) |
EP (1) | EP0790972B1 (en) |
JP (1) | JPH10509450A (en) |
CA (1) | CA2205227A1 (en) |
DE (1) | DE69517535D1 (en) |
WO (1) | WO1996015090A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996015091A1 (en) * | 1994-11-14 | 1996-05-23 | Thiokol Corporation | Synthesis of bis(2,2-dinitropropyl)acetal (bdnpa) |
USD424126S (en) * | 1999-05-25 | 2000-05-02 | Hasbro, Inc. | Combination walker/ride-on vehicle for toddlers |
FR2807428A1 (en) * | 2000-04-10 | 2001-10-12 | Agency Defense Dev | ENERGETIC PLASTICIZER COMPRISING BIS (2,2-DINITROPROPYL) FORMAL AND BIS (2,2-DINITROPROPYL) DIFORMAL, AND PROCESS FOR PREPARING THE SAME |
US6425966B1 (en) | 1999-09-15 | 2002-07-30 | Alliant Techsystems Inc. | Energetic plasticizer, and explosive and propellant composition containing same |
US6620268B2 (en) * | 2000-04-10 | 2003-09-16 | Agency For Defense Development | Energetic plasticizer comprising eutetic mixture of bis (2,2-dinitropropyl) formal, 2,2-dinitropropyl 2,2-dinitrobutyl formal and bis (2,2-dinitrobutyl) formal, and preparation method thereof |
US20090216049A1 (en) * | 2006-04-20 | 2009-08-27 | Dimension Technology Chemical Systems, Inc. | Process and intermediates for the production of BDNPA and BDNPF and other bis(dinitroalkyl)acetals and formals |
Citations (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1312186A (en) * | 1919-08-05 | Albert theodore king | ||
US2227128A (en) * | 1940-02-06 | 1940-12-31 | Standard Oil Dev Co | Chemical composition |
US2388409A (en) * | 1943-04-10 | 1945-11-06 | Harvel Res Corp | Reaction products of secondary aliphatic alcohol and formaldehyde and methods of producing the same |
US2415046A (en) * | 1944-04-21 | 1947-01-28 | Commercial Solvents Corp | Acetals of nitro alcohols |
US2519540A (en) * | 1950-08-22 | Bianufacttjre of dietbnbl acetal | ||
US2535458A (en) * | 1950-12-26 | Production of formals | ||
US2875252A (en) * | 1959-02-24 | Preparation of acetone ketals | ||
US3288863A (en) * | 1963-09-30 | 1966-11-29 | Thomas N Hall | Polynitrodiol and method of preparation |
US3291833A (en) * | 1963-11-29 | 1966-12-13 | Aerojet General Co | Nitroacetals |
US3523808A (en) * | 1963-11-29 | 1970-08-11 | Aerojet General Co | Nitroacetal compounds |
US3526667A (en) * | 1962-02-15 | 1970-09-01 | Us Navy | Process for acetal preparation |
US3629338A (en) * | 1964-07-06 | 1971-12-21 | Aerojet General Co | Certain fluoro-containing nitro-acetal compounds |
US4048219A (en) * | 1974-04-17 | 1977-09-13 | The United States Of America As Represented By The Secretary Of The Navy | Acetals derived from negatively substituted aldehydes and polynitro- or halonitroethanols |
US4062897A (en) * | 1974-04-17 | 1977-12-13 | The United States Of America As Represented By The Secretary Of The Navy | Acetals derived from negatively substituted aldehydes and polynitro- or halonitroethanols |
US4374241A (en) * | 1982-01-29 | 1983-02-15 | The United States Of America As Represented By The Secretary Of The Navy | Nitropolyformals |
US4453021A (en) * | 1982-12-27 | 1984-06-05 | The United States Of Americaas Represented By The Secretary Of The Navy | Dinitropropyl fluorodinitroethyl formal plasticizer and method of preparation |
US4756777A (en) * | 1987-04-03 | 1988-07-12 | The United States Of America As Represent By The Secretary Of The Navy | Bis(2,2,2-fluorodinitroethoxy)-(1,1,1-fluorodinitro-2-propoxy)methane |
US4841075A (en) * | 1986-12-11 | 1989-06-20 | Japan Tobacco, Inc. | Method of preparing acetal or ketal |
US4997499A (en) * | 1984-05-22 | 1991-03-05 | The United States Of America As Represented By The Secretary Of The Navy | Bis (dinitropropyl) formal/dinitrobutyl dinitropropyl formal plasticizer |
-
1994
- 1994-11-14 US US08/339,140 patent/US5449835A/en not_active Expired - Lifetime
-
1995
- 1995-09-08 EP EP95933058A patent/EP0790972B1/en not_active Expired - Lifetime
- 1995-09-08 JP JP8516028A patent/JPH10509450A/en active Pending
- 1995-09-08 CA CA002205227A patent/CA2205227A1/en not_active Abandoned
- 1995-09-08 DE DE69517535T patent/DE69517535D1/en not_active Expired - Lifetime
- 1995-09-08 WO PCT/US1995/011371 patent/WO1996015090A1/en active IP Right Grant
Patent Citations (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2519540A (en) * | 1950-08-22 | Bianufacttjre of dietbnbl acetal | ||
US2535458A (en) * | 1950-12-26 | Production of formals | ||
US2875252A (en) * | 1959-02-24 | Preparation of acetone ketals | ||
US1312186A (en) * | 1919-08-05 | Albert theodore king | ||
US2227128A (en) * | 1940-02-06 | 1940-12-31 | Standard Oil Dev Co | Chemical composition |
US2388409A (en) * | 1943-04-10 | 1945-11-06 | Harvel Res Corp | Reaction products of secondary aliphatic alcohol and formaldehyde and methods of producing the same |
US2415046A (en) * | 1944-04-21 | 1947-01-28 | Commercial Solvents Corp | Acetals of nitro alcohols |
US3526667A (en) * | 1962-02-15 | 1970-09-01 | Us Navy | Process for acetal preparation |
US3288863A (en) * | 1963-09-30 | 1966-11-29 | Thomas N Hall | Polynitrodiol and method of preparation |
US3291833A (en) * | 1963-11-29 | 1966-12-13 | Aerojet General Co | Nitroacetals |
US3523808A (en) * | 1963-11-29 | 1970-08-11 | Aerojet General Co | Nitroacetal compounds |
US3629338A (en) * | 1964-07-06 | 1971-12-21 | Aerojet General Co | Certain fluoro-containing nitro-acetal compounds |
US4048219A (en) * | 1974-04-17 | 1977-09-13 | The United States Of America As Represented By The Secretary Of The Navy | Acetals derived from negatively substituted aldehydes and polynitro- or halonitroethanols |
US4062897A (en) * | 1974-04-17 | 1977-12-13 | The United States Of America As Represented By The Secretary Of The Navy | Acetals derived from negatively substituted aldehydes and polynitro- or halonitroethanols |
US4374241A (en) * | 1982-01-29 | 1983-02-15 | The United States Of America As Represented By The Secretary Of The Navy | Nitropolyformals |
US4453021A (en) * | 1982-12-27 | 1984-06-05 | The United States Of Americaas Represented By The Secretary Of The Navy | Dinitropropyl fluorodinitroethyl formal plasticizer and method of preparation |
US4997499A (en) * | 1984-05-22 | 1991-03-05 | The United States Of America As Represented By The Secretary Of The Navy | Bis (dinitropropyl) formal/dinitrobutyl dinitropropyl formal plasticizer |
US4841075A (en) * | 1986-12-11 | 1989-06-20 | Japan Tobacco, Inc. | Method of preparing acetal or ketal |
US4756777A (en) * | 1987-04-03 | 1988-07-12 | The United States Of America As Represent By The Secretary Of The Navy | Bis(2,2,2-fluorodinitroethoxy)-(1,1,1-fluorodinitro-2-propoxy)methane |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996015091A1 (en) * | 1994-11-14 | 1996-05-23 | Thiokol Corporation | Synthesis of bis(2,2-dinitropropyl)acetal (bdnpa) |
US5648556A (en) * | 1994-11-14 | 1997-07-15 | Thiokol Corporation | Synthesis of bis(2,2-dinitropropyl)acetal (BDNPA) |
USD424126S (en) * | 1999-05-25 | 2000-05-02 | Hasbro, Inc. | Combination walker/ride-on vehicle for toddlers |
US6425966B1 (en) | 1999-09-15 | 2002-07-30 | Alliant Techsystems Inc. | Energetic plasticizer, and explosive and propellant composition containing same |
FR2807428A1 (en) * | 2000-04-10 | 2001-10-12 | Agency Defense Dev | ENERGETIC PLASTICIZER COMPRISING BIS (2,2-DINITROPROPYL) FORMAL AND BIS (2,2-DINITROPROPYL) DIFORMAL, AND PROCESS FOR PREPARING THE SAME |
US6592692B2 (en) | 2000-04-10 | 2003-07-15 | Agency For Defense Development | Energetic plasticizer comprising bis(2,2-dinitropropyl) formal and bis(2,2-dinitropropyl) diformal, and preparation method thereof |
US6620268B2 (en) * | 2000-04-10 | 2003-09-16 | Agency For Defense Development | Energetic plasticizer comprising eutetic mixture of bis (2,2-dinitropropyl) formal, 2,2-dinitropropyl 2,2-dinitrobutyl formal and bis (2,2-dinitrobutyl) formal, and preparation method thereof |
US20090216049A1 (en) * | 2006-04-20 | 2009-08-27 | Dimension Technology Chemical Systems, Inc. | Process and intermediates for the production of BDNPA and BDNPF and other bis(dinitroalkyl)acetals and formals |
Also Published As
Publication number | Publication date |
---|---|
WO1996015090A1 (en) | 1996-05-23 |
JPH10509450A (en) | 1998-09-14 |
DE69517535D1 (en) | 2000-07-20 |
EP0790972A1 (en) | 1997-08-27 |
EP0790972A4 (en) | 1998-01-28 |
EP0790972B1 (en) | 2000-06-14 |
CA2205227A1 (en) | 1996-05-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5739325A (en) | Hydrogenolysis of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-Hexaazatetracyclo 5.5.0.05,9.03,11 !dodecane | |
EP0603382A1 (en) | Process for making high purity hydroxylammonium nitrate | |
US5449835A (en) | Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) | |
US5648556A (en) | Synthesis of bis(2,2-dinitropropyl)acetal (BDNPA) | |
US4476322A (en) | Synthesis of dimethylmethylene dinitramine | |
JPH022888B2 (en) | ||
Blomquist et al. | N-Nitrosoacylarylamines as Catalysts in Addition Polymerization1 | |
US4419155A (en) | Method for preparing ternary mixtures of ethylenediamine dinitrate, ammonium nitrate and potassium nitrate | |
US6177033B1 (en) | Nitration of organics in carbon dioxide | |
US4087469A (en) | Method of producing 2,2 '-methylenebis(4,6-dialkylphenols) | |
US5354924A (en) | Process for the production of dinitrotoluene | |
CA1340073C (en) | Process for the production of dinitrotoleune or mononitrobenzene | |
EP0471043A4 (en) | ||
US3356714A (en) | 4-fluoro-4, 4-dinitrobutyric acids and esters thereof | |
US3472889A (en) | Aminonitriles | |
RU2012563C1 (en) | Method of cellulose nitrate producing | |
EP0053400B1 (en) | Process for preparing malononitrile | |
JP2001151718A (en) | Method for producing tertiary butoxybenzene derivative | |
RU2111957C1 (en) | Method of synthesis of 3-chloro-2-hydroxypropyltrimethylammonium chloride | |
RU2106338C1 (en) | Method of preparing dinitrotoluene | |
US2831835A (en) | Fluoropropiolyl fluoride and polymers thereof | |
SU490288A3 (en) | The method of obtaining salt 1,1 "-di / oxyalkyl / -4,4" bipyridyla | |
US4876387A (en) | Process for preparing 2,4,5-trifluorobenzoic acid | |
USH447H (en) | Synthesis of 1,3,5-trinitro-1,3,5-triazacyclohexane | |
SU1735290A1 (en) | Method of n-methylmorpholine-n-oxide synthesis |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: THIOKOL CORPORATION, UTAH Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HAMILTON, R. SCOTT;WARDLE, ROBERT B.;REEL/FRAME:007330/0317 Effective date: 19950103 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
AS | Assignment |
Owner name: CORDANT TECHNOLOGIES, INC., UTAH Free format text: CHANGE OF NAME;ASSIGNOR:THIOKOL CORPORATION;REEL/FRAME:011712/0322 Effective date: 19980423 |
|
AS | Assignment |
Owner name: THE CHASE MANHATTAN BANK, NEW YORK Free format text: PATENT SECURITY AGREEMENT;ASSIGNOR:ALLIANT TECHSYSTEMS INC.;REEL/FRAME:011821/0001 Effective date: 20010420 |
|
AS | Assignment |
Owner name: ALLIANT TECHSYSTEMS INC., MINNESOTA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:THIOKOL PROPULSION CORP.;REEL/FRAME:012343/0001 Effective date: 20010907 Owner name: THIOKOL PROPULSION CORP., UTAH Free format text: CHANGE OF NAME;ASSIGNOR:CORDANT TECHNOLOGIES INC.;REEL/FRAME:012391/0001 Effective date: 20010420 |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
AS | Assignment |
Owner name: ALLIANT TECHSYSTEMS INC., MINNESOTA Free format text: RELEASE OF SECURITY AGREEMENT;ASSIGNOR:JPMORGAN CHASE BANK (FORMERLY KNOWN AS THE CHASE MANHATTAN BANK);REEL/FRAME:015201/0095 Effective date: 20040331 |
|
AS | Assignment |
Owner name: BANK OF AMERICA, N.A., NORTH CAROLINA Free format text: SECURITY INTEREST;ASSIGNORS:ALLIANT TECHSYSTEMS INC.;ALLANT AMMUNITION AND POWDER COMPANY LLC;ALLIANT AMMUNITION SYSTEMS COMPANY LLC;AND OTHERS;REEL/FRAME:014692/0653 Effective date: 20040331 |
|
FEPP | Fee payment procedure |
Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 12 |
|
AS | Assignment |
Owner name: BANK OF AMERICA, N.A., CALIFORNIA Free format text: SECURITY AGREEMENT;ASSIGNORS:ALLIANT TECHSYSTEMS INC.;AMMUNITION ACCESSORIES INC.;ATK COMMERCIAL AMMUNITION COMPANY INC.;AND OTHERS;REEL/FRAME:025321/0291 Effective date: 20101007 |
|
AS | Assignment |
Owner name: BANK OF AMERICA, N.A., CALIFORNIA Free format text: SECURITY AGREEMENT;ASSIGNORS:ALLIANT TECHSYSTEMS INC.;CALIBER COMPANY;EAGLE INDUSTRIES UNLIMITED, INC.;AND OTHERS;REEL/FRAME:031731/0281 Effective date: 20131101 |
|
AS | Assignment |
Owner name: ORBITAL ATK, INC., VIRGINIA Free format text: CHANGE OF NAME;ASSIGNOR:ALLIANT TECHSYSTEMS INC.;REEL/FRAME:035753/0373 Effective date: 20150209 |
|
AS | Assignment |
Owner name: ALLIANT TECHSYSTEMS INC., VIRGINIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036815/0330 Effective date: 20150929 Owner name: ORBITAL ATK, INC. (F/K/A ALLIANT TECHSYSTEMS INC.) Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036815/0330 Effective date: 20150929 Owner name: COMPOSITE OPTICS, INC., CALIFORNIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036815/0330 Effective date: 20150929 Owner name: FEDERAL CARTRIDGE CO., MINNESOTA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036815/0330 Effective date: 20150929 |
|
AS | Assignment |
Owner name: ORBITAL ATK, INC. (F/K/A ALLIANT TECHSYSTEMS INC.), VIRGINIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036816/0624 Effective date: 20150929 Owner name: ORBITAL ATK, INC. (F/K/A ALLIANT TECHSYSTEMS INC.) Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036816/0624 Effective date: 20150929 Owner name: EAGLE INDUSTRIES UNLIMITED, INC., MISSOURI Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036816/0624 Effective date: 20150929 Owner name: AMMUNITION ACCESSORIES, INC., ALABAMA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036816/0624 Effective date: 20150929 Owner name: ALLIANT TECHSYSTEMS INC., VIRGINIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036816/0624 Effective date: 20150929 Owner name: FEDERAL CARTRIDGE CO., MINNESOTA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:BANK OF AMERICA, N.A.;REEL/FRAME:036816/0624 Effective date: 20150929 |
|
AS | Assignment |
Owner name: NORTHROP GRUMMAN INNOVATION SYSTEMS, INC., MINNESOTA Free format text: CHANGE OF NAME;ASSIGNOR:ORBITAL ATK, INC.;REEL/FRAME:047400/0381 Effective date: 20180606 Owner name: NORTHROP GRUMMAN INNOVATION SYSTEMS, INC., MINNESO Free format text: CHANGE OF NAME;ASSIGNOR:ORBITAL ATK, INC.;REEL/FRAME:047400/0381 Effective date: 20180606 |